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Highly Selective Reaction of α-Halo-α,β-unsaturated Esters with Ketones or Aldehydes Promoted by SmI2: An Efficient Alternative Access to Baylis-Hillman Adducts

José M. Concellón* and Mónica Huerta

*Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, C/Julián Clavería 8, 33071 Oviedo, Spain, Email: jmcguniovi.es

J. M. Concellon, M. Huerta, J. Org. Chem., 2005, 70, 4714-4719.

DOI: 10.1021/jo0504969 (free Supporting Information)


Abstract

The samarium diiodide promoted addition of α-halo-α,β-unsaturated esters to carbonyl compounds led to (Z)-2-(1-hydroxyalkyl)-2,3-alkenoates in good yields and very high stereoselectivity. A mechanism is proposed to explain this transformation.

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Key Words

Samarium, Additions, Baylis-Hillman adducts


ID: J42-Y2005-560